


Pretty in Pink

by His_French_Girl



Category: Supernatural
Genre: Canon Divergence, Friendship, Gender Identity, Human Castiel, Implied Castiel/Dean Winchester, Implied Relationships, M/M, Romantic Friendship, cross-dressing
Language: English
Status: Completed
Published: 2016-04-24
Updated: 2016-04-24
Packaged: 2018-06-04 06:49:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,736
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6646207
Author URL: https://archiveofourown.org/users/His_French_Girl/pseuds/His_French_Girl
Summary: <blockquote class="userstuff">
              <p>When Castiel becomes human, Sam and Dean take him to get a new wardrobe. As Castiel experiences making his own choices, his friends learn that the clothes don't always make the man. Soon Dean and Sam are helping to feed Castiel's penchant for pink.</p>
            </blockquote>





	Pretty in Pink

**Author's Note:**

> Edited by Bryre
> 
> This story was inspired by some of the pictures that Misha Collins has posted on Twitter and Facebook. Anyone who has seen him in the yellow waitress uniform will understand.

For as long as the Winchesters had know Castiel, he always wore the same thing: his suite with a white shirt and tie, and his ever present trench coat. Now that he was human, Sam and Dean thought that it would be a good idea to take Castiel out to get a new wardrobe. They took him to the thrift store and told him he could get whatever he wanted, except for socks, underwear and shoes, which they would get him new. 

Cas walked along the aisles of clothing racks, examining things that caught his eye and checking to find his size. Sam insisted that he and Dean hang back and just watch as the former angel picked what he wanted. Castiel placed his choices in the cart that he had grabbed in anticipation of his shopping spree. Eventually the cart contained the usual jeans, t-shirts and button down shirts that Cas saw his friends wear. He also added a couple of sweaters and a hoodie for the colder weather. 

Cas continued wandering among the aisles and ended up in the women's section. Castiel looked at the pastel and patterned shirts and added a pink one to his cart. Dean blinked and stared, and was about to step forward when his younger brother held him back with a hand on his arm.

“He's getting chick clothes,” Dean protested, shrugging the hand away. 

“Leave him be,” Sam warned, leaning back against one of the displays and folding his arms across his chest. “We told him he could get whatever he wanted.”

“But he's a dude, and he's getting dresses.”

“So, he needs to figure things out on his own. If he likes it, what harm will it do?”

“But he's a dude.”

Sam glared at his brother, but didn't say anything else. Dean sighed, muttering something under his breath, but didn't make a move to stop Cas. When Castiel was finally satisfied with his selections, he pushed his cart over to the brothers.

“Are you finished, Cas?” Sam asked with a casual look at the cart's contents.

The dark haired man nodded. “Yes, I believe that I have chosen enough clothing to do for a while. I even found some things that will be suitable for the colder season.”

“That's good Cas,” Sam responded. “Why don't you show us what you picked out.” 

Castiel smiled shyly and proceeded to show the brothers each article that he had selected. He noticed that Dean frowned when he held up a long burgundy skirt.

“Dean, you look displeased.”

“What? No.” Dean protested quickly, but Cas was aware that the other man made a concerted effort to avoid eye contact, even though he added, “It's fine, if that's what you want.”

“Sam?” Cas turned to the younger Winchester, confused. “Are my choices not acceptable?”

“Well, it's just that some of the things you picked are for women.” Sam explained gently. “But if you really like it, you should get it.”

Cas looked down at the clothes. He had been happy while he was picking out things that he liked, but now he felt embarrassed. 

“I see.” He looked at the floor as he spoke, unable to look at the brothers. “I will put the items that are feminine back.” 

“No, wait, Cas.” Dean put his hand on the shopping cart to stop Castiel from turning it around to return the clothes. “Sam's right. If you like it, you should get it. To hell with what people think. What else you got in there?”

Cas looked at Dean carefully. He didn't see any negative emotions displayed on Dean's face. He turned to Sam, who smiled at him. Cas hesitantly showed the brothers the rest of the items. 

“Whoa, whoa, whoa, hold on,” Dean exclaimed when Castiel produced a mustard yellow dress. “Put that one back.” 

Cas looked at Dean quizzically while Sam glared at his brother.

“What's wrong with it?” Cas asked hesitantly, studying the dress he held.

“For one thing, it's a waitress uniform,” Dean explained, then made a face. “And it's ugly. That colour doesn't look good on anyone.”

Dean took the offending garment from Cas and gave it to Sam to put back on the rack. Dean then pulled out a light pink blouse and held it up to Cas.

“Huh...” Dean looked at the blouse critically. “Actually, that colour might not look too bad on you. Not sure about that other dress, though. It's a darker pink. But it might be okay.”

Sam turned away to hide his smile, while Cas beamed at Dean. 

“What?” Dean looked at his brother. 

“I didn't say anything.” Sam turned away again and snickered. Castiel seemingly ignored the exchange in favour of taking the dress in question out of the cart to look at. 

“I like the colour,” Cas stated simply and placed it decisively back in the cart.

“It's okay, Cas.” Sam turned back to their friend. “As long as you like it, that's all that matters.”

Once Cas had returned the waitress uniform, and was happy with the rest of his choices, he wheeled the shopping cart to the cash and Sam paid for his purchases. Back at the bunker, Sam helped Castiel sort the clothes to put in the wash, showing him how to check the labels to make sure that nothing would need to go to the dry cleaners. Dean made dinner and for the rest of the evening, everyone did their own quiet activities. The topic of Castiel's choice in clothing did not come up again.

 

A few days later, the pink blouse made it's debut. Sam watched his brother to make sure that Dean wouldn't be an insensitive ass and say anything that would hurt their friend's feelings. Sam was pleasantly surprised when the only comment Dean made to Castiel about the article of clothing was something that the fallen angel could take as a compliment.

“That colour works on you, Cas.” Dean walked over to his friend and pulled on the shirt until the bottom that had been so carefully tucked in hanged out of Castiel's jeans. 

“Looks better untucked," Dean explained, then walked away without another word. Cas smiled and continued what he was doing. No further comments were made.

 

Two days later, the burgundy skirt was paired with a black sweater. Nothing was said, until Dean found Sam alone and Dean made a seemingly offhand remark.

“He needs some better shoes to go with his clothes,” was all that Dean said before, once again, the matter was dropped.

 

Over the next few weeks, Castiel's wardrobe grew. Sam helped Castiel place an order for some accessories from an online specialty store. A few days later, pair of low heeled pink pumps and a pair of black flats made their way into the bunker. The pumps went perfectly with the pink dress that Castiel seemed to favour wearing. Sam or Dean took him back to the thrift store a few more times to look for more things that he liked. Soon Castiel was wearing pale pink pyjamas with fuzzy pink slippers when they had a movie night, and his favourite pink blouse during the days at the bunker.  
Dean brought home a pink sweater set and a pink nightgown for Castiel after one of his supply runs. Sam had noticed the interest Cas had shown while walking through the women's lingerie section at a department store and had gone back to the website where he had ordered the shoes. There was a section of lingerie designed specifically for men, and soon Cas had a collection of camisoles and panties to wear under his regular clothing. 

Out in public, Castiel still wore men's clothing. The were more practical and more comfortable when hunting, but he had a preference for wearing more feminine clothing, especially anything pink, when he was hanging around the bunker.

“Hey Cas,” Dean greeted the angel one morning when Castiel entered the kitchen in search of coffee. Cas was wearing the pink nightgown, along with heeled, feathered slippers Dean had gotten for him on a whim.

“Good morning, Dean.” Cas poured himself a cup of coffee and joined Dean at the table.

“So you like the slippers, then?” Dean tried to sound casual, trying to hide the happiness he felt that Cas liked the gift.

“Yes, I do, very much.” Castiel lifted his feet to look at the slippers. They were pink satin, open toed and had soft pink feathers on the top. They were the right size and matched the frothy, flowing nightgown perfectly. 

“I'm glad. I thought you might like them, to go with that nightgown.” Dean blushed and looked down at his cup. “I, uh, I know you aren't interested in wearing makeup, but I got you something else. Cause you like pink.”

Dean reached into the pocket of his jeans and pulled something out. He placed a tube of pink lipstick and a bottle of pale pink nail polish on the table in front of Castiel. Cas looked at the items, then looked up at Dean, his eyes moist.

“Thank you, Dean.” 

“You're welcome.” Dean smiled at him tentatively. 

Castiel stood and walked over to Dean, leaning down to kiss his cheek.

“Thank you for accepting me without trying to force me into human norms.”

Dean blushed again. He stood up and looked into Cas' eyes while he spoke.

“Cas, I know that angels aren't hung up on things like gender. It doesn't matter if you're in a dude's body, Raphael ended up taking a female vessel, so whether you were in a male or female vessel, you're still you. I just want you to be happy and comfortable with who you are. That's all that matters.”

Castiel gently kissed Dean on the lips. When he pulled back, Dean took his hand.

“I love you, Cas.”

“And I you, Dean.”

Castiel squeezed Dean's hand before letting go to leave the room. Dean remained standing silently for a few seconds, before taking his seat again. Sam came in and got a cup of coffee. He sat down where Cas had been sitting and saw the lipstick and nail polish still on the table. He didn't say a word - not even when Castiel came rushing back into the kitchen, grabbed the cosmetics off the table, and trailed his fingers over a blushing Dean's shoulder as he went past. Sam just smiled.


End file.
